US4122110A - Process for manufacturing alcohols, particularly linear saturated primary alcohols, from synthesis gas - Google Patents

Process for manufacturing alcohols, particularly linear saturated primary alcohols, from synthesis gas Download PDF

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US4122110A
US4122110A US05/846,486 US84648677A US4122110A US 4122110 A US4122110 A US 4122110A US 84648677 A US84648677 A US 84648677A US 4122110 A US4122110 A US 4122110A
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process according
catalyst
alcohols
cobalt
alkali metal
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Andre Sugier
Edouard Freund
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IFP Energies Nouvelles IFPEN
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
    • B01J23/86—Chromium
    • B01J23/868—Chromium copper and chromium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/847—Vanadium, niobium or tantalum or polonium
    • B01J23/8472—Vanadium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/889—Manganese, technetium or rhenium
    • B01J23/8892—Manganese
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/1512—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by reaction conditions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
    • C07C29/156—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • the present invention relates to a catalytic process for manufacturing saturated straight-chain primary alcohols from carbon monoxide and hydrogen.
  • the processes of the Fischer and Tropsch type have poor selectivity, as well as concerns the nature of the products as the repartition of the molecular weights for a given type of products, and they have poor productivity, usually lower than 5 kg/m 3 of catalyst/hour for a given alcohol.
  • Another known process is the isobutyl synthesis used in Europe between 1935 and 1945; it is analogous to the methanol synthesis and utilizes the same catalyst (zinc chromite) modified by addition of an alkali metal salt, at high pressures and temperatures (respectively 300 to 400 bars, 380° to 450° C.).
  • a representative composition of the main products obtained is the following: methanol (50%), isobutanol (20-40%), n-propanol and higher alcohols; the latter comprise non-linear primary and secondary alcohols (50--50%).
  • French Pat. No. 1,074,045 proposes the use of precipitated catalysts comprising a major proportion of copper and a minor proportion of metal of the iron group with possible addition of known activators, such as alkali metals, zinc or chromium; a copper, iron, potassium catalyst is described.
  • THE SELECTIVITY TO LINEAR SATURATED PRIMARY ALCOHOLS IN C 2 or more is often higher than 70% by weight, which differs from the alcohols obtained by isobutyl synthesis.
  • the productivity is great, higher than 100 kg of C 2 + alcohols per cubic meter of catalyst per hour, as compared to 20 kg/m 3 /hour of C 1 -C 4 alcohols for the Fischer - Tropsch method.
  • the pressure is usually between 20 and 250 bars and preferably between 50 and 150 bars
  • the ratio H 2 /CO, CO 2 is advantageously between 0.4 and 10 and preferably between 0.5 and 4 and the temperature is between 150° and 400° C. and preferably between 220° and 350° C.
  • the catalysts which are used according to the invention contain at least 4 essential elements, i.e. copper, cobalt, a third metal M selected from chromium, iron, vanadium and manganese and a fourth metal which is an alkali metal A, preferably lithium, sodium or potassium. Zinc is optional. These elements are in the following atomic proportions: Cu x Co y M z A v (I).
  • x may range from 0.1 to 1, y from 0.1 to 1, z from 0.2 to 1, u from 0 to 0.5 and not above 0.5y, and v represents 0.001 to 0.25 times the sum (x + y + z).
  • x may range from 0.1 to 1, y from 0.1 to 1, z from 0.2 to 1, u from 0 to 0.5 and not above 0.5y, and v represents 0.001 to 0.25 times the sum (x + y + z).
  • the Cu, Co, M and eventually Zn metals are usually present as oxides such as CuO, CoO, CrO 3 or heat decomposable salts such as carbonates, sulfates, nitrates, oxalates, tartrates, citrates, acetates or succinates, or in the form of complexes, for example a chromate or vanadate.
  • oxides such as CuO, CoO, CrO 3
  • heat decomposable salts such as carbonates, sulfates, nitrates, oxalates, tartrates, citrates, acetates or succinates, or in the form of complexes, for example a chromate or vanadate.
  • a method of manufacture which leads to catalysts of higher selectivity and which is thus to be preferred, comprises the manufacture of a common solution of the Cu, Co an M metal compounds with the addition of an agent selected from the organic complexant compounds, preferably from:
  • organic acids with 2 or more acid groups for example oxalic, malonic, succinic or glutaric acid,
  • acid-alcohols for example glycolic, lactic, malic, tartric or citric acid,
  • aminoacids for example aminoacetic acid, alanine or leucine.
  • Water is evaporated from the resulting solution, for example by heating at 200°-600° C., which yields a powder which is agglomerated, preferably with an aluminous cement containing alumina and lime in the form of calcium aluminate.
  • Metal A may be supplied with the other metals, in the form of a soluble salt, or thereafter to the powder or to the formed catalyst.
  • Shaping may be effected according to conventional techniques of the art, particularly by tabletting or extrusion, or by pill-forming while adding, for example, aluminous refractory cements which, further to their binding properties, have a co-catalytic effect due to their basicity.
  • the preferred aluminous cements contain 40-85% b.w. of Al 2 O 3 and 15-30% of CaO with optionally small amounts of other components.
  • Alumina and lime are present in major portion in the form of calcium aluminates.
  • Drying and calcination for example at about 400° to 1000° C., are the usual final steps.
  • the incorporation of the alkali metal(s) may occur before shaping of the catalyst or thereafter, for example by impregnation with a solution of soluble salts or hydroxides of one or more elements of the group Ia of the periodic classification. This addition may also take place before the drying and calcining steps by addition of a solution of one or more soluble compounds of metals of group Ia; it may also take place with chromates or dichromates of one or more elements of group Ia.
  • the resulting catalyst is in the form of oxides with the metals present in the following relative proportions:
  • 450 ml of water are added to a mixture of 160 g of chromic anhydride CrO 3 with 483 g of copper nitrate Cu(NO 3 ) 2 , 3 H 2 O and 233 g of cobalt carbonate 2 CoCO 3 , 3 Co(OH) 2 , n H 2 O containing 50.5% b.w. of cobalt; when the gas evolution has ceased, 100 g of citric acid are added.
  • the resulting solution is dried at 200° C. for 2 hours and then heated in air for 3 hours at 450° C.
  • the other half of the powder is admixed in totality with a refractory aluminous cement of the "Super Secar" type of composition in % b.w.: Al 2 O 3 : 81, CaO: 17, Na 2 O: 0.8, Fe 2 O 3 : 0.1, plus others.
  • This mixture is obtained from 70% of powder obtained according to the above method and 30% of aluminous cement.
  • the resulting mixture is then made to 5 mm pills in a pill-maker by pulverization of a 5% b.w. aqueous solution of potassium hydroxide, so that the potassium content, expressed as K 2 O, of the resulting product is 1.7% b.w.
  • the pills are then heated in air for 2 hours at 400° C.; the resulting catalyst B 2 contains metals in the following molar proportions: Cu 1 Co 1 Cr 0 .8 K 0 .09 + aluminous cement.
  • the product is dried for 2 hours at 200° C. and then heated in air at 450° C. for 2 hours.
  • the resulting powder is made to tablets of 5 ⁇ 5 mm size.
  • Catalyst B 3 is thus obtained, where the metals are present in the following molar proportions:
  • 450 ml of water and 100 g of citric acid are added to a mixture of 160 g chromic anhydride CrO 3 , 483 g copper nitrate Cu (NO 3 ) 2 3 H 2 O, 163 g cobalt carbonate of 50.5% b.w. cobalt content and 37.6 g zinc carbonate ZnCO 3 .
  • the resulting solution is dried for 2 hours at 200° C. and then treated for 2 hours at 450° C.
  • the resulting powder is made to 5 ⁇ 5 mm tablets and then impregnated with a potassium hydroxide solution to introduce 2% b.w. of potassium, expressed as K 2 O.
  • the tablets are then treated for 2 hours at 400° C.
  • the resulting catalyst C contains the metals in the following molar proportions:
  • Catalyst D One third of the powder is impregnated with a solution containing 1.6 mole of manganese nitrate and then dried at 200° C. and treated 2 hours at 450° C. The resulting powder is made to 5 ⁇ 5 mm tablets which are impregnated with a solution of potassium hydroxide, so as to introduce 2% b.w. of K 2 O. After a 2 hours treatment at 400° C., there is obtained catalyst D where the metals are present in the following molar proportions:
  • catalyst E One third of the powder is impregnated with a solution containing 1.6 mole of iron nitrate and then dried at 200° C. and heated in air for 2 hours at 450° C. The resulting powder is made to tablets and impregnated with potassium hydroxide and heat treated as catalyst D; the resulting catalyst E has the molar composition:
  • catalyst F The last third of the powder is impregnated with a solution containing 1.6 mole of ammonium vanadate and then dried at 200° C. The resulting powder is shaped, impregnated with potassium hydroxide and heat treated as the catalysts D and E. Catalyst F is thus obtained; its molar composition is Cu Co V 0 .8 K 0 .12.
  • catalyst E' The procedure is as for catalyst D', except that manganese nitrate is replaced by 646 g of iron nitrate Fe (NO 3 ) 3 , 9 H 2 O.
  • the resulting catalyst E' has the same composition as catalyst E.
  • the activity of the so-prepared catalysts for the synthesis of linear primary alcohols from mixtures of CO, CO 2 and H 2 is determined as the amount, expressed as grams per hour and per gram of catalyst, of the products obtained by passing a gas mixture of the composition:
  • Vvh volume (NTP) of the reactants per hour and per volume of catalyst.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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US05/846,486 1976-10-29 1977-10-28 Process for manufacturing alcohols, particularly linear saturated primary alcohols, from synthesis gas Expired - Lifetime US4122110A (en)

Applications Claiming Priority (2)

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FR7633046 1976-10-29
FR7633046A FR2369234A1 (fr) 1976-10-29 1976-10-29 Procede de fabrication d'alc

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AU (1) AU508915B2 (enExample)
DE (1) DE2748097C3 (enExample)
FR (1) FR2369234A1 (enExample)
GB (1) GB1547687A (enExample)
PL (1) PL107649B1 (enExample)
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Cited By (78)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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US4301253A (en) * 1980-09-25 1981-11-17 Union Carbide Corporation Process for the selective production of ethanol and methanol directly from synthesis gas
US4333852A (en) * 1980-09-25 1982-06-08 Union Carbide Corporation Catalyst for the selective production of ethanol and methanol directly from synthesis gas
US4346179A (en) * 1979-04-05 1982-08-24 Institut Francais Du Petrole Production of alcohols from synthesis gases
US4377643A (en) * 1981-12-21 1983-03-22 The Standard Oil Company Upgrading synthesis gas
US4391701A (en) * 1980-04-09 1983-07-05 Institut Francais Du Petrole Process for upgrading heavy oils
US4440668A (en) * 1982-07-06 1984-04-03 Mobil Oil Corporation Catalyst for the conversion of synthesis gas to higher alcohols
US4442228A (en) * 1978-10-24 1984-04-10 Hoechst Aktiengesellschaft Process for the manufacture of ethanol from synthesis gas
US4476247A (en) * 1981-12-21 1984-10-09 The Standard Oil Company Synthesis gas catalyst
US4478955A (en) * 1981-12-21 1984-10-23 The Standard Oil Company Upgrading synthesis gas
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US4537909A (en) * 1984-02-28 1985-08-27 Phillips Petroleum Company Alcohol synthesis
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CN102041020A (zh) * 2009-10-13 2011-05-04 中国石油化工股份有限公司 流化床费托合成重质烃的方法
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